The filing comes days after the longtime Trump associate was ordered to pay the sum in a defamation case.
Rudy Giuliani, a longtime associate of former President Donald Trump, has filed for bankruptcy just days after he was ordered to pay $148m (£116m) in a defamation case.
He was ordered to pay the sum after a judge found he defamed two Georgia election workers over false claims they tampered with votes in 2020.
Mr Giuliani listed debts as high as $500m and assets of $10m in the filing.
A spokesman said the move should “be a surprise to no one”.
In a statement quoted by US media outlets including the New York Times, spokesman Ted Goodman, said “no person could have reasonably believed that [Mr Giuliani] would be able to pay such a high punitive amount”.
He added that the bankruptcy filing in New York on Thursday would give Mr Giuliani the “opportunity and time to pursue an appeal, while providing transparency for his finances under the supervision of the bankruptcy court”.
Mr Giuliani, 79, said earlier this year that he was having financial difficulties because of his increasing legal fees and expenses.
Last week, an eight-person jury ordered Mr Giuliani to pay $20m to Georgia poll workers Ruby Freeman and her daughter Wandrea “Shaye” Moss.
They were also awarded more than $16m each for emotional distress. Another payment of $75m in punitive damages was ordered to be split between them.
The pair had originally sought between $15m and $43m in damages from Mr Giuliani, Mr Trump’s former personal lawyer.
Addressing reporters outside the court after he was ordered to pay the sum, Mr Giuliani said: “I don’t regret a damn thing.”
The court filling lists nearly 20 creditors, including Ms Freeman, Ms Moss and Hunter Biden, who sued him in September.
Other creditors include the Internal Revenue Service (IRS) and two voting software companies that sued Mr Giuliani over his false claims of election fraud.
A law firm that previously represented Mr Giuliani, Davidoff Hutcher & Citron LLP, is also included. The firm sued Mr Giuliani for $1.4m in unpaid legal fees in September.
Mr Giuliani still faces an indictment in Georgia on racketeering and conspiracy charges as well as a $10m lawsuit by a former business associate over sexual harassment claims.